Thermal isomerization of abietic acid

Takeda, Hiroshi; Schuller, Walter H.; Lawrence, Ray V.

doi:10.1021/jo01268a095

Cited by 26 publications

(21 citation statements)

References 1 publication

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“…We also found that after high dosage irradiation (2.5 megarad), the level of palustric acid in the wood decreased significantly, while the level of dehydroabietic acid greatly increased (data not shown). This phenomenon may be attributed to isomerization which easily happens for RAs with two conjugated double bonds (Takeda et al 1968). Similar observations have been reported with the behavior of Pinus elliottii RAs during seasoning (Quinde and Paszner 1991).…”

Section: Discussionsupporting

confidence: 81%

Identification and Quantification of Nonvolatile Lipophilic Substances in Fresh Sapwood and Heartwood of Lodgepole Pine (Pinus contorta Dougl.)

Gao¹,

Chen²,

Breuil³

1995

HFSG

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Content and composition of lipophilic extractives from fresh sapwood and heartwood of lodgepole pine (Pinus contorta Dougl.) were investigated by solid-phase extraction, GC and GC-MS techniques. The acetone extractive content in sapwood was 1.9-2.2% of oven dry wood, among which were included 1.1-1.3% triglycerides, 0.02-0.03% free fatty acids, 0.3-0.4% free resin acids, 0.15-0.21% steryl esters and waxes, 0.02 % monoglycerides, and 0.02-0.03 % sterols, fatty alcohols and diglycerides. A considerably higher amount of extractives was present in heartwood, i.e., 10-12%, including 0.6-0.7 % triglycerides, 0.8-1.1% free fatty acids, 4.0-5.6% free resin acids, 0.25-0.33 % steryl esters and waxes, 0.4-0.5% monoglycerides, and 0.08-0.1% sterols, fatty alcohols and diglycerides. The most abundant fatty acid residues in the wood triglycerides were oleic (18:1), linoleic (18:2), linolenic (18.-3) and palmitic (16:0) acids. Together they formed about 85 % and 65 % of the total fatty acid composition in the sapwood and heartwood triglycerides, respectively. Of the steryl esters and waxes, 18:2 was the most dominant residue, followed by 18:3 and 18:1. Twelve major free fatty acids and seven free resin acids were identified and quantified. The abundant free fatty acids in both sapwood and heartwood were 18:2 and 18:1, making up 32-41 % and 24-28 % of the total fatty acid amount, respectively. Palustric acid was the dominant free resin acid, its relative proportion to the total resin acids was 52 % in the outer sapwood and 29% in the inner heartwood. Other major resin acids detected included abietic, isoabietic, dehydroabietic, neoabietic acids.

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Section: Discussionsupporting

confidence: 81%

Identification and Quantification of Nonvolatile Lipophilic Substances in Fresh Sapwood and Heartwood of Lodgepole Pine (Pinus contorta Dougl.)

Gao¹,

Chen²,

Breuil³

1995

HFSG

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“…Temperature investigation (Fig. 3E) showed a response increase from 70 • C to 90 • C and a slight decrease after 95 • C, revealing the instability of resin acids at the high temperature [27]. Fig.…”

Section: Optimization Of Derivatizationmentioning

confidence: 90%

“…Scheme of ultrasonic-assisted closed in-syringe extraction and derivatization (UCSED) technique (1: ultrasonic-assisted trace extraction and 2: in-syringe ultrasonicassisted derivatization) and the derivatization process between the two analytes (abietic acid and dehydroabietic acid) and fluorescence reagent 2-(2-(anthracen-10-yl)-1H-naphtho [2,3-d]imidazol-1-yl) ethyl-p-toluenesulfonate (ANITS). [27] and thus may lead to inaccurate results. High performance liquid chromatography (HPLC) coupled with ultraviolet/diode array detection (UV/DAD) [4,[28][29][30][31][32], fluorescence detection (FLD) [29][30][31][32] or MS [25,26,31,33] has been extensively developed, acting as more accurate alternative to GC for analytes susceptible to high temperature.…”

Section: Introductionmentioning

confidence: 99%

Development of ultrasonic-assisted closed in-syringe extraction and derivatization for the determination of labile abietic acid and dehydroabietic acid in cosmetics

Liu

et al. 2014

Journal of Chromatography A

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“…The production of epoxy resin binders from rosin typically follows a DielsAlder reaction with acrylic acid or maleic anhydride, again targeting the levopimaric acid isomer, or a reaction with formaldehyde [141,145,152,153]. The modified rosin is then further functionalized with a base-catalyzed esterification with epichlorohydrin to produce a functional analog to fossil-based epoxies [145,153].…”

Section: Epoxy Resins From Rosinmentioning

confidence: 99%